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First Total Syntheses of Tetracenomycins C and X
Author(s) -
Sato Shogo,
Sakata Keiichiro,
Hashimoto Yoshimitsu,
Takikawa Hiroshi,
Suzuki Keisuke
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201707099
Subject(s) - stereocenter , aryne , isoxazole , chemistry , benzoin , ring (chemistry) , stereoselectivity , acetal , total synthesis , stereochemistry , oxide , medicinal chemistry , enantioselective synthesis , organic chemistry , catalysis
The first total syntheses of tetracenomycins C and X were achieved, featuring 1) preparation of a hexasubstituted naphthonitrile oxide by successive benzyne cycloadditions and an oxidative ring‐opening reaction; 2) a novel ortho ‐quinone mono‐acetal as the A‐ring unit; 3) construction of three contiguous stereogenic centers by an asymmetric benzoin cyclization, an isoxazole oxidation, and a stereoselective reduction.